I don't know. I guess because girls can easy wear guy's stuff and look ok while guys just don't look right in a skirt, not all of them, at least. But I'm a girl and I'm biased so I don't think my answer counts.

I think its alright if you suit it. Like if a muscled, tan guy was wearing a frilly pink dress my first reaction would be, "=.=...you look....nice?" It all depends on body type I guess..and if you look good. Other than that I'm fine with it.

Didn't you see the hipster pictures on pulse a while back? Guys can dress like girls, but they can expect to be made fun of if they do. The reason behind it is probably because traditionally men don't wear makeup or dresses, but women can get away with it because all they're doing is not wearing makeup or dresses. In a way, makeup and dresses are additional aspects of a woman's look, if they're taken away a woman can still appear feminine, but by putting makeup and a dress on, a man is trying to appear feminine even though he is not. That is why it isn't as accepted. It's similar to seeing a woman with facial hair or overly hairy arms and legs. Technically there isn't anything wrong with it, but as a society we've become accustomed to certain attributes being masculine or feminine.

I think girls just tend to look better in both fashion and guys look better in longer clothes.
But it's what we are used to; guys used to wear clothes like dresses
and I think a guy in a kilt is sexy sexy Speedo, hairy legs and all!

well when a girl wears a guys clothes, its considered as "oh she's a tom boy" but if a guy were to wear girls clothing he would be considered gay, and i mean what guy wants to wear girls clothes and have to go throught something like that? but i mean if my boyfriend or one of my guy friends decides hes ready to rock a murse, mandles, a kilt and a nice blouse in public ill think the dude has some major balls, ans hes comfertable with his sexuality

Who knows... Maybe because most ppl in the world are just so narrow minded... Peanut butter has to go with jelly, and ketchup with mustard... It can't be peanut butter with ketchup or jelly with mustard....

You know, I still don't know. My assumption is that most of the clothing taboos are still in place regarding men because a man in a dress defies the laws of masculinity. A lot of men that I've talked to, especially via semi-anon polling, have admitted to having issues with women wearing mens pants and so forth. They prefer women in dresses because they think it's beautiful.

I've seen boys that look like 'hot' girls when they dress up and wear make up. O_O On a japanese TV show but it was long ago. I mean literally jaw dropping. They looked better than most girls
Heck I even have some of my friends and random people say I look like a girl sometimes. ¬.¬ I'm obviously a boy.